
Ski-in/Ski-out holiday rentals in Western Massachusetts
Find and book unique ski-in/ski-out homes on Airbnb
Top-rated ski-in/ski-out rentals in Western Massachusetts
Guests agree: These ski-in/ski-out homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Western Massachusetts ski-in/ski-out rentals
Ski-in/ski-out house rentals

Private chalet tucked in the green mountains

The Pinnacle House at Otis Ridge Ski Area!

Summit View Ski and Golf Retreat w/hot tub & Sauna

Rustic home near skiing & lakes, walk to downtown

FULLY renovated 1 bed/1 bath ski in-out condo!

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

Family Lodge at Jiminy Peak - Pools & Adventure

Sundance Village- Ski-on/off, Hot tub, clubhouse
Family-friendly, ski-in/ski-out home rentals

Mountainside Condo Ski on/off

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

Luxe Ski Getaway Base of Jiminy

The 1799 Farmhouse at the base of Pat's Peak

Modern Mount Snow Gnarvana | Walk to Lifts & Lodge

Ski Mountain Snow&Stratton

4BD 2BA | Mount Snow VT | Ski-Back Trail | Shuttle
Ski-in/ski-out cabin rentals

Beautiful Art Studio with hot tub/sauna #1 Airbnb

Stone's Camp on Stamford Stream

The Run-In - Beautiful Country Cabin with Hot Tub

Green Mt Getaway: <30m to Dining Parks Mountains

Summit Retreat:2BR/2Bath Rustic Beauty + Yoga Room

Blackberry Cottage

Cabin: Private Hot Tub, Walk to Pats Peak Ski Area
Destinations to explore
- Plainview Holiday rentals
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- Rentals with beach access Western Massachusetts
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- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Bash Bish Falls State Park
- Bushnell Park
- Brimfield State Forest
- Norman Rockwell Museum
- Bigelow Hollow State Park
- Kent Falls State Park
- Wintonbury Hills Golf Course
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Dinosaur State Park
- Mount Tom State Reservation
- Albany Center Gallery
- Bousquet Mountain Ski Area
- Hartford Golf Club
- Beartown State Forest
- Mount Snow Ski Resort
- Talcott Mountain State Park
- Huck Finn’s Playland, Albany
- Hancock Shaker Village
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation